Attempts were made to synthesise a conformationally restricted
analogue of kainic acid wherein the double bond was confined
in a ring-system. The stratagem involved an intramolecular
Diels-Alder reaction but could not be tested as the precursors
to the cycloaddition reaction could not be prepared.
Attempts were made to develop a general route to kainic acid
and analogues by employing a 1,3-dipolar cycloaddition reaction
between aziridines and olefins. Triazolines were used as a
precursor to aziridines because of the ease of formation from
alkyl azides and olefins. The required dipolar cycloaddition
was found to occur but produced various side-products from the
triazoline thermolysis. The subsequent Grignard reaction on
the cycloaddition product gave problems as the compound epimerised
under basic conditions and did not undergo reaction with methyl
Grignard or methyl lithium.
An attempt to prepare kainic acid and analogues by an intramolecular
1,3-dipolar cycloaddition or a 1,3-sigmatropic shift
reaction failed when the basic precursors for the reaction could
not be prepared.

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